Oxidative N-Heterocyclic Carbene-Catalyzed γ-Carbon Addition of Enals to Imines: Mechanistic Studies and Access to Antimicrobial Compounds

Peng Cheng Zheng; Jiajia Cheng; Shihu Su; Zhichao Jin; Yu Huang Wang; Song Yang; Lin Hong Jin; Bao An Song; Yonggui Robin Chi

doi:10.1002/chem.201501632

Oxidative N-Heterocyclic Carbene-Catalyzed γ-Carbon Addition of Enals to Imines: Mechanistic Studies and Access to Antimicrobial Compounds

Peng Cheng Zheng, Jiajia Cheng, Shihu Su, Zhichao Jin, Yu Huang Wang, Song Yang, Lin Hong Jin, Bao An Song^*, Yonggui Robin Chi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

Abstract

The reaction mechanism of the γ-carbon addition of enal to imine under oxidative N-heterocyclic carbene catalysis is studied experimentally. The oxidation, γ-carbon deprotonation, and nucleophilic addition of γ-carbon to imine were found to be facile steps. The results of our study also provide highly enantioselective access to tricyclic sulfonyl amides that exhibit interesting antimicrobial activities against X. oryzae, a bacterium that causes bacterial disease in rice growing.

Original language	English
Pages (from-to)	9984-9987
Number of pages	4
Journal	Chemistry - A European Journal
Volume	21
Issue number	28
DOIs	https://doi.org/10.1002/chem.201501632
Publication status	Published - Jul 1 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Organic Chemistry

Keywords

antimicrobial activity
enals
N-heterocyclic carbenes
organocatalysis
reaction mechanisms
γ-carbon addition

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10.1002/chem.201501632

Cite this

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abstract = "The reaction mechanism of the γ-carbon addition of enal to imine under oxidative N-heterocyclic carbene catalysis is studied experimentally. The oxidation, γ-carbon deprotonation, and nucleophilic addition of γ-carbon to imine were found to be facile steps. The results of our study also provide highly enantioselective access to tricyclic sulfonyl amides that exhibit interesting antimicrobial activities against X. oryzae, a bacterium that causes bacterial disease in rice growing.",

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AU - Zheng, Peng Cheng

AU - Cheng, Jiajia

AU - Su, Shihu

AU - Jin, Zhichao

AU - Wang, Yu Huang

AU - Yang, Song

AU - Jin, Lin Hong

AU - Song, Bao An

AU - Chi, Yonggui Robin

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KW - enals

KW - N-heterocyclic carbenes

KW - organocatalysis

KW - reaction mechanisms

KW - γ-carbon addition

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Oxidative N-Heterocyclic Carbene-Catalyzed γ-Carbon Addition of Enals to Imines: Mechanistic Studies and Access to Antimicrobial Compounds

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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